Try This On: Hollis Wong-Wear in Helmut Lang, SJP, Hunter Boots and More

Studies show shopping is at least 12 times more fun en masse. Our Try This On series is all about the camaraderie of sartorial group projects.

A.L.C. lace crop top | ASTR textured skirt | SJP leather pumps | Shiraleah embellished wool clutch

Of all celebrated occasions and festive dates, New Year’s Eve expects the most out of your outfit. Especially if you’re going to be in New York City, and especially if you’re writer/singer/style icon Hollis Wong-Wear.

No, the Seattle-based GRAMMY nominee and Macklemore collaborator isn’t performing in the final moments of 2014—or at least there are no plans for such a thing as of yet. But wouldn’t “always be prepared—and dressed!—for anything” be a good New Year’s resolution? And one to enact early? We took Wong-Wear into the dressing rooms of our Downtown Seattle store to dial in three versions of ready-to-go ready-to-wear to kick off 2015.

“The last few New Year’s Eves, I’ve been performing,” Wong-Wear told me. “But this is the first year for a while that I’ll just be out and about—in NYC, no less!—so I’m excited to dress a little more like myself. And since I’ll be on the town, my outfit has to be practical through subway rides and walks between bars—I’m gonna hop around, naturally.”

But “practical” never has to mean boring. It can mean casual knee-highs with your not-too-tall heels, and an ultra-vivid mash-up of color and texture as a sort of wow-factor exchange for the short, tight, shiny and/or embellished go-to party-dress style.

Wong-Wear was into it. “Why not make hot pink chic?” she mused. “It’s a tall order, but I feel really stylish in this.”

Of course, “practical” can always mean ultra sensible—without sacrificing a thing. In other words, all hail the all-weather ankle boot revolution.

3.1 Phillip Lim tunic (see similar Phillip Lim styles in embellished gold and peplum detail | Lafayette 148 New York skirt | Hunter high-heeled Chelsea boots | Topman knit hat

“I was surprised I liked this look so much; the splattered skirt isn’t something I would ever pick for myself, but the top is awesome and super comfy. And I love wearing my glasses as an accessory,” says our party gal.

Playing with the idea of statement necklaces, our final look was all about taking a different tack with bling. We started with the necklaces and went from there, adding a slinky-but-cozy knit minidress layered over a little peek of floral.

Helmut Lang knit tunic | Topshop crop top (worn under tunic) | Ella necklaces (available in downtown Seattle only; see similar statement necklace styles online  or visit the Nordstrom near you for in-store exclusives)

“I can see myself dancing in this dress and being comfortable all night,” says Wong-Wear. Which sounds like a pretty great way to inaugurate the new year.


Follow Hollis Wong-Wear on Instagram

Shop: New Year’s Eve dresses | Designer dresses | Dresses under $150 | Women’s outfit ideas

Images by Elizabeth Rudge

—Laura Cassidy